Squire – Company Overview

Squire is a booking and payment platform that connects people with great barbers nationwide. Squire makes it easy to discover and book the best barbers wherever you are, in just a few taps.

Squire is also the premier management platform for barbershops. Using Squire, barbers are able to engage their customers, process bookings and payments and better market their business through Squire’s “barbershop discovery” capabilities. Fully integrated with a point of sale, inventory management and payroll systems, Squire is a one-stop solution for barbershop owners to efficiently operate their business. 

With headquarters in New York and a presence in major cities in the United States and Canada, Squire has quickly become a market leader in technology solutions for the barbershop industry nationwide.

Reid Christian, an investor at Charles River Ventures (CRV) who was part of the Series B, said that he knew Squire would be a success when he experienced the product at Rust Belt Barbering in Buffalo, New York. Christian compared Squire to a “Venmo-like experience” with transactions. He estimates billions of dollars in men’s grooming spend.

When shops broadly reopen, Squire is in a good, timely spot to be adopted by the masses. For the co-founders, the incoming wave of interest was affirmed a long time ago. For more information, please visit getsquire.com or download the Squire iOS app from the App Store.

The Role: Vice President of Marketing

The Vice President of Marketing will report to Co-founder / CEO Songe LaRon. The VP Marketing will be a dynamic, visionary, highly quantitative leader. The ideal candidate has extensive experience in key aspects of B2B marketing and a deep understanding of the customer in the SMB segment. This executive must work well cross-functionally and have a track record of successfully scaling marketing efforts in a growth-oriented company. This individual will have consistently overachieved in high-growth environments and actively contributed to building high-performance marketing organizations. It will be critical that this individual has been a part of scaling a rapidly growing, high velocity customer acquisition model by developing B2B marketing campaigns to drive qualified leads, position the organization to go after targeted buyers, and use those campaigns and messages to scale revenues.

The VP Marketing will lead all efforts in the areas of campaign operations, demand generation, ABM, partner marketing, brand marketing, content marketing, event marketing, and email while partnering with sales, operations, and product leaders to execute on a comprehensive go-to-market program. This executive will be strategically-oriented, quantitatively-focused, and a solid operator, able to achieve operational efficiency at scale. Additionally, (s)he must have an expert understanding of sales pipeline, key drivers, and the role of marketing at each stage of the funnel.  

To truly succeed in this role, the ideal candidate will be exceptional at understanding the key drivers of B2B marketing objectives. He/she must possess have a strong ability to prioritize and build alignment to reach marketing/sales objectives across the go-to-market organization. This person will need to get into the details and work with others to deeply understand what drives great results, campaign success and customer insights. This leader must have a keen eye for talent, and have the ability to build a strong team, culture, and growth-oriented environment. Ultimately, this executive will be strategic while also taking a very hands-on approach to get things done.


  • Lead all marketing initiatives for Squire, and oversee the hiring and development of the marketing organization
  • Work alongside the executive team to continue to build a strong and well-defined brand
  • Provide leadership and oversight of our Marketing team, developing the strategic and operational framework to ensure ongoing success and company growth objectives
  • Build and manage best-in-class B2B Marketing/demand gen programs and optimization of Lead to Opportunity funnel
  • Develop and evaluate key performance metrics; provide senior leadership accurate summaries and analysis of campaigns, results, and forecasts
  • Provide strategic guidance, insight, and knowledge about market trends, consumer attitudes, competitors, and the effectiveness of the marketing strategy
  • Foster continuous improvement; ensure that all marketing activities are efficient, effective, and scalable
  • Develop and maintain a regular communication cadence with leadership
  • Keep our team apprised of changing policies, competitive developments, and industry/market trends
  • Partner with Sales to ensure alignment on strategy, resources, and KPIs
  • Enable a growing sales team with compelling sales decks, 1-pagers, and sales materials
  • Create and maintain comprehensive metrics reports of our lead generation marketing campaigns, campaign efficiency, and insights on future optimizations
  • Oversee the strategy of a constant stream of content marketing and thought leadership programs/materials
  • Own key metrics within Marketing Operations, including marketing performance measurement, budgeting, strategic planning, process definition, and marketing systems & data


  • A proven leader and motivator with an entrepreneurial spirit – unafraid to roll-up sleeves, get it done, and "lead from the front”
  • At least 8 years’ experience of B2B marketing, with at least 4+ years in a leadership position
  • Expertise in marketing to the SMB economy sector
  • Success growing the marketing organization for an early stage SaaS company that has seen growth to $50M or more in annual revenue
  • Deep experience in all demand gen channels including: SEM, SEO, email, content syndication, lifecycle marketing, etc.
  • Ability to execute on and lead a team across all aspects of marketing
  • Experience building scalable and repeatable processes for the marketing organization
  • Past delivery of an iterative approach to refining and helping build an analytically-driven marketing function
  • Strong analytical skills, proven ability to consume and understand data, work with data scientists and analysts to get to clear results and analysis to drive optimization
  • Exceptional skills in verbal and written communications; must also be an excellent listener
  • Proven ability to successfully articulate and address complex business issues and opportunities

Personal Characteristics

The VP Marketing must bring intellectual, professional, and personal values that complement the team. This executive will be an extremely smart and dynamic individual with outstanding communication skills and a balanced ego. They will be intellectually curious and have a true passion for their craft. This person will be team-oriented, always focused on what’s right for the business, not just the individual or function. (S)he will possess an ability to build deep relationships and earn the respect of other teams.

A strong, decisive and action-oriented leadership style will be necessary, as this leader will make, communicate, and take accountability for timely decisions. The candidate must thrive in fast-paced, constantly changing environments and be able get to the heart of issues rapidly and act decisively. The VP Marketing will be a strategic thinker who possesses exceptional interpersonal skills to share the key financial drivers with the entire organization. (S)he must be a proven leader who creates strong morale, good spirit in their team and brings fun to the workplace, while sharing wins and successes and fostering open dialogue. Above all, this leader must have a “roll up your sleeves and get your hands dirty” attitude, doing whatever it takes to get the job done.

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